Thioureido N-acetyllactosamine derivatives as potent galectin-7 and 9N inhibitors
Research output: Contribution to journal › Article
Abstract
Derivatives of N-acetyllactosamine carrying structurally diverse thioureido groups at galactose C3 were prepared from a C3'-azido N-acetyllactosamine derivative in a three-step reaction sequence involving azide reduction and isothiocyanate formation by thiophosgene treatment of the C3-amine, followed by reaction of the isothiocyanate with a panel of amines. Evaluation of the N-acetyllactosamine thioureas as inhibitors against galectins-1, 3, 7, 8N (N-terminal domain), and 9N (N-terminal domain) revealed thiourea-mediated affinity enhancements for galectins-1, 3, 7, and 9N. In particular, good inhibitors were discovered against galectin-7 and 9N (K-d 23 and 47 mu M, respectively, for a 3-pyridylinethylthiourea derivative), which represents more than an order of magnitude affinity enhancement over the parent natural N-acetyllactosamine. (c) 2005 Elsevier Ltd. All rights reserved.
Details
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Research areas and keywords | Subject classification (UKÄ) – MANDATORY
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Original language | English |
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Pages (from-to) | 1215-1220 |
Journal | Bioorganic & Medicinal Chemistry |
Volume | 14 |
Issue number | 4 |
Publication status | Published - 2006 |
Publication category | Research |
Peer-reviewed | Yes |
Bibliographic note
The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Division of Microbiology, Immunology and Glycobiology - MIG (013025200), Organic chemistry (S/LTH) (011001240)